Drake - When To Say When & Chicago Freestyle (Music video and Lyrics)

“Chicago Freestyle” released simultaneously with Drizzy’s “When To Say When.” Drake dedicates his lyrics to the lessons he learned on his come-up and reflects on the various mistakes he made in his past relationships.

The title’s usage of a city seemingly marks a new addition to Drake’s AM/PM series, which contains similar elements. This marks Drizzy’s first addition to the mini grouping since June 2016’s “4PM in Calabasas,” as he continues to revisit his past and focuses on lyricism.

While Drake is from Toronto, Canada and has no official connection to Chicago, it is likely that Drizzy recorded the single in the “Windy City,” as his AM/PM series typically were named based on location.

Drake - When To Say When & Chicago Freestyle04:42

Chorus: Giveon

Two thirty baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is, whenever I visit
Windy city, she blowing me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

Verse 1: Drake

Ayy, truck to the plane, to the truck
Truck to the hotel lobby
Me, I go through underground garages
It's presidential suite, on deposit
Elevator up to the room
Shower up and then we hit the club
Touchdown, gotta see what's up
Area code in my phone
What numbers do I still have?
Who do I know from the past?
Hit one, she say she got a man
Hit another one, it goes green
Must've changed phones on the team
'Member when you lead me in between?
That was 2017
All good, Chubbs'll look around
Find one that seem my type
That my dawg and he know what I like
He done found me plenty in my life
Problem is, I meet a girl tonight
Then I go and treat her too nice
Galleria credit card swipes
I don't even know if she a wife

Pre-Chorus: Drake

But I do know one thing though
Women they come they go
Saturday, through Sunday, Monday
Monday through Sunday, yo
Maybe I'll love you one day
Maybe we'll someday grow
'Til then I'll sit my drunk ass on that runway
On this one way

Chorus: Giveon

Two thirty baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is, whenever I visit
Windy city, she blowing me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

Verse 2: Drake

Jewelry in the safe on arrival
Pistol on J for survival
Lot of people gunning for the title
Lot of people trying to take us viral
I'm just trying to have a nice night, though
Waiter brought the check for the meal
She said, "Babe, I think there was a typo"
Nah girl, I got it, that's light though
I could show you bigger things than that
It's gon' be a minute 'till I'm back
Let me give you images that last
AMEX had a limit in the past
I had plenty women in the past
I done plenty sinnin' in the past
You don't need to know, but you can ask
Stickin' on your backstage pass
All access 'cause you bad
You could go wherever with that ass
Show, to the shower, to the truck
Truck, to the club, for the party
You go in first with your girls
'Cause I don't know who's out there watching

Pre-Chorus: Drake

But I do know one thing though
Women they come they go
Saturday, through Sunday, Monday
Monday, Sunday, yo
Maybe I'll love you one day
Maybe we'll someday grow
'Till then I'll sit my drunk ass on that runway
On this one way

Chorus: Giveon

Two thirty baby, won't you meet me by The Bean?
Too early, maybe later you can show me things
You know what it is, whenever I visit
Windy city, she blowing me kisses, no
Thirty degrees, way too cold, so hold me tight
Will I see you at the show tonight?
Will I see you at the show tonight?

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